Chelsea Handler is reflecting on one of her worst real estate purchases.
The multi-hyphenate entertainer called out Robert F. Kennedy Jr. and his wife, Cheryl Hines, for selling her a nightmare home in 2021.
Chelsea Handler reportedly bought the couple’s old home in Brentwood, Los Angeles, for $5.9 million. It featured five bedrooms, a pool, and a whole lot of problems for the comedian.
Chelsea Handler Recalls Purchasing A Nightmare Home From RFK Jr. And Cheryl Hines
Handler slammed RFK Jr. and Hines on the latest episode of her “Dear Chelsea” podcast, revealing that she had not lived on the property for years due to structural issues. She recalled a home inspector describing the Brentwood house as “the most toxic environment.”
“That’s how f-cked up this house was, the idea that this guy is in charge of the health of our country when he didn’t even have a proper foundation at his house,” Handler lamented, referencing RFK Jr.’s status as secretary of the U.S. Department of Health and Human Services (HHS).
“I’m not exaggerating any of this. It was a disaster, and I didn’t know it going in because everything was, you know, under wraps,” Handler continued. She added that at least three people told her the home was “cursed,” and there was an illegal outdoor storage unit on the property.
The Former ‘Chelsea Lately’ Host Slammed The Couple’s Audacity
After realizing the home she purchased was a nightmare that would drain more from her account, Handler could not help but be pissed with the little note Hines left. The “Curb Your Enthusiasm” actress allegedly wrote, “Let us know if there’s anything we can do for you, Chelsea.”
“I’m like, ‘Yeah, how about a f-cking foundation?’ That’s something you could do for me,” Handler retorted, shocked by Hines’ audacity to leave a note. The podcast host added that she wasn’t “angry” anymore and had gotten over the horrible real estate experience.
Handler is well-known for her real estate investments and has several properties in her portfolio. The Brentwood house isn’t the only terrible real estate investment she has made, with Handler recalling a major financial mistake in 2025.
The Comedian Regretted Her Attempt To Stop Long Family Visits
The Blast reported in August 2025 that Handler had opened up about the consequences of trying to stop her family from overstaying their welcome. She revealed in an interview with MarketWatch that she had once converted a five-bedroom home into a two-bedroom.
Handler explained that she made the changes to stop her family from getting too comfortable during their visits, as a two-bedroom would push them to leave early instead of staying over. She confirmed that the property conversion was her biggest money mistake.
According to Handler, she had to reconvert the home to a five-bedroom to sell it because a two-bedroom was not profitable when she listed the property on the market. Naturally, the two conversions drained more money from her account, making it a major financial mistake.
The Media Personality Moved Into A Zen Rental Home
Although Handler did not specify which of her properties had been transformed, her words seemed to hint at her longtime Bel Air home. The New York Post reported that she sold the stunning property for $10.5 million in 2021 and moved into an 18,000-per-month rental in the same neighborhood.
The rental was described as a Zen-themed property with five bedrooms and four baths. It featured a harmonious indoor-outdoor flow with park-like grounds, a courtyard, and a separate casita alongside the main house. The home was also where Handler lived when she rekindled her romance with Jo Koy.
The pair reportedly knew each other for decades, starting as close friends before their relationship turned romantic. The outlet claimed their love started budding during their days on Handler’s E! talk show “Chelsea Lately,” where Koy frequently appeared as a guest.
Chelsea Handler Prioritized Herself Over Her Relationship With Jo Koy.
During the good times with Koy, Handler once raved about him being the love of her life and implored fans not to give up on finding love regardless of their age. As it turned out, Handler had more love for herself than Koy, and she chose to prioritize her happiness.
The Blast covered the story in February 2025, reporting that Handler opened up about her separation from Koy in a candid interview. She explained that it felt like she had to choose between having a relationship and prioritizing herself and her sanity.
Handler believed that continuing her romance with Koy would ultimately compromise everything she stood for, which was not a path she could consider. “When I realized it wasn’t going to work out, I was able to end it in a healthy, mature way,” she added.